


The Best Night of My Life

by ninaloveshiddles



Category: SPN, Supernatural
Genre: Alternate Universe - Pre-Canon, Best Friends, Blow Job, Chubby, Cunnilingus, F/M, Friends to Lovers, Kissing, Love Confessions, Making Love, Making Out, Mild Hurt/Comfort, Oral Sex, Stanford University, Vaginal Sex, insecure, pudgy
Language: English
Status: Completed
Published: 2015-06-28
Updated: 2015-06-28
Packaged: 2018-04-06 15:07:27
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,496
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4226490
Author URL: https://archiveofourown.org/users/ninaloveshiddles/pseuds/ninaloveshiddles
Summary: <blockquote class="userstuff">
              <p>Prompt from whiskeyxnightmare  Stanford AU. Sam and the reader are best friends. He has no idea that she has an enormous crush on him. She won’t tell him because she is insecure about her chubbiness and doesn’t want to get rejected. One night she lets the secret slip, and Sam proceeds to give her the best night of her life.</p>
            </blockquote>





	The Best Night of My Life

**Author's Note:**

  * For [whiskeyxnightmare](https://archiveofourown.org/gifts?recipient=whiskeyxnightmare).



> Hope this is what you wanted. I'm sorry it took so long, work and Summer classes hit me hard last week lol.

**Good luck tonight! I’m sure it will be great :)** You look down and read the message from Sam on your phone and give a small sigh. You have a date tonight, and you feel like shit. You should be happy; the guy was really cute, but you had your eye on someone else.

 **Thanks, Sam! I’ll need it…** You text back. Sam Winchester is your best friend in the entire world. You met him at freshman orientation, and the two of you have been inseparable since. He was the best guy in the world; intelligent, sweet, kind…drop dead gorgeous. The truth is, you’re in love with him. Ever since you met him, you knew he was special. Something about him was different from all other guys you had met, like he was destined for so much more He had opened up to you about his past, the way his dad traveled, and the older brother Dean, who you could tell he secretly idolized. It was hard not to fall for someone you were so close to; especially when they looked like that.

You look in the mirror, checking your dress and make up. You fight the urge to grab at your stomach; and you suck in as much as you can, trying to look thinner. That’s why you never told Sam about your true feelings. You were chubby and it made you feel insecure around the Winchester. Why would he go for a chubby, plain girl like you when he could have a skinny nurse, or a gorgeous education major? You don’t stand a chance with him, and that’s why you’re going on this date. You need to get over Sam Winchester.

 

You sit in the restaurant twiddling your thumbs as you wait for your date. You are surprisingly excited in spite of yourself. It’s been a while since someone had been interested in you, and you feel the butterflies begin to beat their wings inside your rib cage. The waiter comes by and you order a water, needing to quench your sudden thirst. A small smile is at your lips as you realize that this could be a really good evening. A new opportunity with a decent guy. And you get to keep Sam as your best friend; win- win right? Not to mention the guy kind of looked like Sam, brunette hair, light eyes, taller than you… this could work out just fine.

_Five Minutes Later_

Well this is kind of boring. You look at your phone to see if he texted you. Nope. Maybe there was traffic? It does get pretty bad this part of town. The waiter asks you if you want to order. You decide to wait a few more minutes; it would be rude, right?

_Ten Minutes Later_

This is normal right? People are late to things. You bite your lip in concern and look down at your phone. 2 messages from Sam and an email. Great.

_Thirty Minutes Later_

You’ve been fighting back tears all evening, but they finally start to seep out. What the hell? You feel completely worthless and sick to your stomach. You actually got stood up! And from a guy who you didn’t even care that much about. You feel your self-esteem plummet as your breathing gets harsh and ragged. You stand up from the table, leaving some cash before you bolt at the door, hot tears stinging your face.

You drive quickly back to campus and walk to your dorm. You rapidly text out a message to Sam. You need your best friend right now.

**Hey, I’m sure you’re busy but if you’re not could you come by? It’s not important or anything, just need a friendly face.**

You slam the door behind you, and crawl onto your bed. Thank god your roommate is out of town, because you really don’t want her to see you cry. You bury your face into the pillow, not bothering to take off your shoes or dress. You feel completely numb, like you barely exist. You let out a small sob. How fucking humiliating and degrading! Your head begins to pounds as your body heaves in sobs. You hear a knock on the door and slowly get up. You try to check your hair and face in the mirror so you don’t look like a total mess. You open the door and are greeted by a smiling Sam, dimples prominent on his cheeks. The light from his eyes fade and are suddenly filled with concern when he sees you.

“Shit” he mutters. “It wasn’t just a bad date was it?” You feel more tears fall down your face and he captures you in a massive hug. “I’m so sorry” he breathes, “what happened?” The two of you walk into the room and hop on your bed to talk, like you’ve done so many times before. You sniffle as you try to explain between gasps.

“He. Didn’t. Show” you manage, trying to control your trembling bottom lip. Sam’s eyes narrow, and he gives a disgusted scowl.

“I’ll kill him” he mutters.

“Ha! Like you’ve ever hurt anything in your life Sam” you mumble, moping in desolation and self-pity.

“Uh, yeah” he says awkwardly, and you can tell he has his lying face on. You make a mental note to address this later. “Come here” he urges. Holding his arms out wide. You hug him tightly, and put your head against his chest, resisting the urge to sniff his sweet scent or nuzzle into his shirt. His chin rests on your head, and he rocks you slightly.

“He’s an asshole. You’re better off without him.”

You let out another sob, staining Sam’s shirt with your tears. “I’m not ever gonna find anyone Sam!”

“Shh, don’t say that-“

“I’m serious! I just feel like I’m not good enough for anyone.”

He squeezes you a little tighter, “trust me, you are.”

You shake your head, “and you know what the funny thing is?” you ask, your head throbbing as your mind feels numb. “I only went out with him because I wanted to get over-” you stop yourself midsentence, your body tensing rigidly.

“Get over…who?” Sam urges, his voice eager and curious. Shit, why the fuck did you say that?

“I meant, umm” you whisper, unable to think of anything quickly. Should you tell him? _No! He’s not going to like you back! That would just completely ruin your friendship._   He lifts your chin up, forcing you to meet his gaze.

“Tell me” he commands, his voice serious. You briefly lose yourself in his hazel eyes. _Oh shit! Brain to mouth, brain to mouth: don’t say anything stupid._

Before you can stop yourself you feel your lips utter “you.” It doesn’t even sound like a word, just a simple noise.

“Me?” he whispers, face confused. This is bad!

“I think you should go” you blurt out, not wanting to continue the awkwardness further. You hop off the bed, but he grabs your wrist.

“Why would you try to get over me?”

You feel your blood begin to boil a bit; you’re flustered and frustrated. Sam isn’t making this any easier for you. “Oh please Sam, like you would ever like a chubby girl. I had to stop liking you because it was never going to go anywhere. Why would it? You would never go for someone like me.” You spit out.  You jerk your arm away from his grasp and storm over to the door. Before you can grab the handle, strong hands are around your waist, and you are spun quickly around.

“Wanna bet?” Sam breathes. He grabs your face and leans in with a firm kiss, his lips crafting perfectly to yours. Your breath hitches, and every muscle stiffens in surprise. Sam Winchester is kissing you! His thumbs are stroking your face! Holy fuck, that’s his tongue! You finally regain your senses and wrap your arms around his neck, reveling in the feel of the way his tongue gently prods your mouth. He breaks the kiss, and gazes intently in your eyes. You stare back, trying to control your breathing. _Words woman! Words!_

“Umm, kissed me. Like me?” _Nailed it._

Sam gives you a shy smile, biting his lip in a way that sets your ovaries on fire.  “Yes. I like you. I have for some time.”

“But, I don’t- why?” You mutter out, your hands absentmindedly stroking his soft brown hair.

“Why wouldn’t I? You’re gorgeous, and sweet. You’re so smart and it’s so easy to be around you. I fell in love with my best friend.” Your draw drops and you are vaguely aware that you have an idiotic grin plastered on your face. “Oh yeah, and I was so mad when I found out you were going on that date. I was praying that you would change your mind.”

You give a soft giggle and squeeze him in a loving embrace, feeling the slight outline of abs under his shirt. He gives you another kiss, this one fierier as you tug down on his bottom lip. He captures your tongue and begins to suck on it, loud and wet. You emit a moan, unable to control yourself. He involuntarily pushes his hips towards you, releasing his own moan as he becomes turned on by your sounds. His hands reach around to your dress, and he unzips it slowly, allowing the fabric to fall and pool at your high heels.

“That was a sexy dress,” he pauses, and holds you at arm’s length as he surveys your body. You squirm uncomfortably, your arms awkwardly covering up your skin. “But I think it looks better off of you” he says genuinely. You give a shy smile, your face blushing bright red. He lifts his shirt over his head, throwing it to the floor. He shimmies out of his pants, leaving his boxers. You gaze at his body, smooth and muscular. You feel every muscle down below clench in want and anticipation. You see that his erection is tenting his pants, and you feel giddy that you could turn on someone as amazing as him.

He grabs you, rubbing his erection at your crotch. He kisses at your throat, leaving nibbles and dark hickeys. “Just in case anyone else tries to ask your pretty ass out” he murmurs into your skin. You grab at his boxers and scoot them down his thighs, grabbing at his now free erection. Holy fuck it’s huge. You knew it would be big, but Jesus Christ! The head is already red, and you know he will start leaking pre cum at any moment. He hisses in pleasure as you run your thumb over the slit, dancing along the top. You grab firmly at the shaft and slowly stroke his thick cock, up and down. His body shivers and he tosses his head back slightly, his hands gripping your arms. He begins to buck slightly into your hand, tying to create more friction and pressure. You get on your knees and thrust his dick into your mouth, letting it hit the back of your throat. He gives a slight yelp, grabbing on to your hair.

“Oh fuck babe.” He says through gritted teeth. You bob your head as you hollow out your cheeks, sucking violently as spit gets everywhere. You moan a little, letting the vibrations dance across his member. “Holy fuck you’re good at this” he moans. His hands rub your back and make their way to your bra strap. He unclasps your bra, and you let it fall off of you. You grab onto his ass, pushing him in further until you deep throat him. “Ahhhh.” He grabs your shoulders and pulls you up to his level. “Bed” he growls, and you quickly go over and lay down, filled with excited energy. He grabs your panties and pulls them down, leaving you completely naked like him.

“So beautiful” he whispers in awe, scanning over your naked form. He leans in between your thighs, and blows soft air against your sex, sending an odd sensation through you. He flicks his tongue across your clitoris, causing your hips to jerk. He gives a small chuckle and sucks at it, just barely grazing his teeth. You let out a high whine, feeling like a wanton lioness. He sticks his tongue inside you, nodding approvingly of how wet you are. He laps it up, twisting and turning inside you as he stretches your walls. Your lower half is practically buzzing in ecstasy. His finger massages your clit in synchronization with his talented tongue.

You arch your back on the bed, trying not to squeeze his head with your thighs, but oh it feels good, too good! You feel like a goddess of carnality and passion. The pure essence of desire. He stops, and you nearly groan at the loss. He crawls over your body.

“(Y/n)?” He whispers.

“Yeah?”

“I really want to have sex with you. I’ve wanted to for so long baby. Is that okay?” He asks carefully, searching your eyes to make sure you’re telling the truth.

“Of course” you whisper, and give him a slow, tender kiss. He gives a happy grin that almost makes you break into laughter. He lines up with you and sinks in slowly, completely spreading you. You moan loudly, a deep delicious burn traveling all around you. He kisses your breasts, teasing your nipples as he thrusts in and out slowly. He keeps a steady pace, making sure not to hurt you or overwhelm you. You both lock eyes and watch as the other becomes increasingly undone. He twists inside you, and you clench around his cock. You writhe about on the bed, the sensation too good to handle

“More” you beg.

“Anything for you baby” he whispers. He increases his pace, and sets on a harder rhythm. The friction against your walls builds you up, and you yelp when he nails your sweet spot. His hands run worshipfully over your body, and he gives deep guttural moans as he moves inside you. You feel your release building up, pressure and ecstasy taking over your entire body. You tip over the edge and cum loudly, every part of your body covered in flames. He cums quickly after you, his hips thrusting erratically as he fills you up. He collapses next to you, grabbing your frame and pulling it towards you. You roll towards him and nuzzle your face into the crook of his neck.

“Wow. You’re amazing.”

“You too” he breathes, still trying to calm down from his orgasm. “I’m so glad this finally happened” he whispers, his smile audible in his voice.

“Oh trust me, it’s happened in my head many times” you admit. He snuggles closer to you.

 “And how does it compare?” he questions.

“Well” you begin, closing your eyes. “It was the best night of my life Sam.”

“Mine too baby. Mine too.”

**Author's Note:**

> Thanks for reading. If you've given me a request in the past week and a half, I promise I have not forgotten you. Life kind of got in the way of my writing :)


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